New N-acylamino acids and derivatives from renewable fatty acids: gelation of hydrocarbons and thermal properties

被引：32

作者：

Duarte, Rodrigo da Costa ^{[1
]}

Ongaratto, Renata ^{[1
]}

Piovesan, Luciana Almeida ^{[1
]}

de Lima, Vania Rodrigues ^{[1
]}

Soldi, Valdir ^{[2
]}

Merlo, Aloir Antonio ^{[3
]}

Montes D'Oca, Marcelo G. ^{[1
]}

机构：

[1] Univ Fed Rio Grande, Escola Quim & Alimentos, Lab Kolbe Sintese Organ, BR-96203000 Rio Grande, RS, Brazil

[2] Univ Fed Santa Catarina, Grp Estudo Mat Polimericos, BR-88040900 Florianopolis, SC, Brazil

[3] Univ Fed Rio Grande do Sul, Lab Sintese Organ & Mat Inteligentes, BR-91501970 Porto Alegre, RS, Brazil

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 19期

关键词：

Low-molecular-weight gelators; Fatty amino acids; L-Serine; Ricinoleic acid; L-ALANINE; DELIVERY; AMIDES; GELS;

D O I：

10.1016/j.tetlet.2012.03.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This work reports the synthesis of new fatty N-acylamino acids and N-acylamino esters from the C16:0, C18:0, C18:1, and C18:1(OH) fatty acid families and demonstrates the activity of these compounds as organogel agents. Compounds were heated and dissolved in various solvents (n-hexane, toluene, and gasoline). Only saturated C16:0 and C18:0 derived from alanine were able to form gels in toluene, and saturated C16:0 derived from phenylalanine showed gelation in n-hexane. This is the first evidence that fatty N-acylamino esters and N-acylamino acid derivatives of L-serine and fatty acids C16:0, C18:0, and C18:1 are able to form gels with hexane. This observation confirms the importance of the hydroxyl group in the segment derivative of L-serine in forming good gels. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：2454 / 2460

页数：7

共 15 条

[1] First report of phase selective gelation of oil from oil/water mixtures. Possible implications toward containing oil spills [J].